CAS 220114-01-2 RuCl2[(S)-xylbinap][(S)-daipen]

Synonyms

RuCl2[(S)-(DM-BINAP)][(S)-DAIPEN], 220114-01-2, Dichloro[(S)-(-)-2,2 inverted exclamation marka-bis[di(3,5-xylyl)phosphino]-1,1 inverted exclamation marka-binaphthyl][(2S)-(+)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II)

IUPAC Name

[(2S)-1-azanidyl-1,1-bis(4-methoxyphenyl)-3-methylbutan-2-yl]azanide;[1-[2-bis(3,5-dimethylphenyl)phosphaniumylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphanium;dichlororuthenium(2+)

Molecular Weight

1221.30

Molecular Formula

C71H74Cl2N2O2P2Ru

InChI Key

CDEJRZFAUMUTIA-OGLOXHGMSA-N

Purity

96%

Storage

2-8°C

Exact Mass

1220.36000

H-Bond Acceptor

H-Bond Donor

Application

RuCl2[(S)-xylbinap][(S)-daipen] serves as a highly effective catalyst specifically designed for the enantioselective hydrogenation of various ketones, particularly those that are sterically unsymmetrical like acetophenone, heteroaryl ketones, benzophenones, cyclopropyl, and cyclohexyl ketones. It enhances enantiomeric excess (ee) through the use of XylBINAP compared to traditional BINAP, functioning optimally by forming effective hydrogen bonds with protic bidentate amines in transition states. This catalyst facilitates the preparation of complex cyclometalated ruthenium derivatives and supports the asymmetric hydrogen transfer between alcohols and carbonyl compounds. It also proves valuable in asymmetric hydrogenation of amino and heteroaromatic ketones. Under conditions involving a strong base, RuCl2[(S)-xylbinap][(S)-daipen] can enable dynamic kinetic resolution of simple ketones with substituents at the α-position to form two chiral centers with high yield. Moreover, it selectively reduces carbonyl groups even in the presence of olefins within a molecule, and it has been noted for its application in synthesizing pharmacologically active oxazolidinones that act as inhibitors for cholesterol absorption by targeting the NPC1L1 ligand.

January 13, 2025

Outstanding Catalyst for Selective Hydrogenation

Using RuCl2[(S)-xylbinap][(S)-daipen] in our research has been remarkable. It provides high enantioselectivity in ketone hydrogenation, ensuring efficient creation of chiral centers, vital for our pharmaceutical applications. Highly recommended for precision in complex chemical syntheses.